Workaholic Hugh Dillon Balances New Album And Tour With High Profile TV Roles

Sound Of Music 2019 – Photo by Corey Kelly

By Keith Sharp

The big question is where the Headstones’ Hugh Dillon finds the time to record a new album,`Flight Risk,’ and plan a 17-date Canadian tour (with two dates in Buffalo) while at the same time completing the second season of The Mayor Of Kingstown TV series with season five of the hit TV show, Yellowstone already in the can.

“I just love what I do,” shrugged Dillon, conducting a lightening quick phone interview from his Toronto residence before jumping into his car to drive back down to Pittsburgh, where he is shooting Season 2 of The Mayor Of Kingstown before taking a breather from in front of the cameras to conduct the Headstones’ tour which kicked off Tuesday, November 22nd and concludes Thursday, December 22nd at Toronto’s Phoenix Concert Theatre.

Headlight Holds A Deer – Directed by Stuart Campbell DOP for Paramount+ Mayor of Kingstown

Although Dillon has been featured in the role of sheriff Donnie Haskell during five seasons of Paramount’s Yellowstone series (starring opposite Kevin Costner) and is now filming his second series as co-creator and executive producer of The Mayor Of Kingstown (featuring Jeremy Renner and Oscar-winning actress Dianne Wiest) also performing in the role of Ian Ferguson, he still professes that his first love is performing in front of his own band.

“You get talking to Kevin Costner and Jeremy Renner and they don’t want to talk about acting, all they want to talk about is music,” professed Dillon. “It’s always been my first love.”

Writing and composing came in handy for Dillon as he rode out the pandemic, spending days in his Montana motel room between snatches of opportunity to film the fifth season of Yellowstone. An unlikely songwriting partner is Taylor Sheridan, a noted actor/producer/director who co-created Yellowstone and worked with Dillon to create The Mayor Of Kingstown, who shared writing credits with Dillon on one track titled “Ashes.”

Track Ashes · Headstones – ‘Flight Risk’

“I never co-write lyrics with anyone else, but I connected with Taylor on that one song,” Dillon allowed. “He found a synergy that worked with me on the production of “Ashes” and that just worked on that song.”

Although music has always come before everything else, Dillon comes by his thespian skills honestly. Ever since making his acting debut in 1995 as murder suspect Clarence Gaskill in Bruce McDonald’s independent movie `Dance Me Outside’, he has appeared in a staggering 19 movies and 23 television shows, Dillon has successfully combined his acting with his musical output, recording a total of 10 studio albums. “(The Tragically Hip’) Gord Downie and I were in the same dramatic art class in high school. I had a teacher there who said I should really get into acting but I felt music was where it was at,” he noted. “I made a decision I wasn’t prepared to be critiqued about my acting. I much preferred to be in my own band, writing my own songs, I need control and I wasn’t getting that as a fucking actor.”

Hugh Dillon - Headstones
Hugh Dillon – Headstones – Photo by The Music Express

Saying that he could have been a criminal, a hockey player (NHL legend Doug Gilmour lived on his street in his native Kingston Ontario) or a musician, Dillon wisely chose the latter, but it was a stint busking and slumming in London England (where he and this writer first met in 1985) that he found himself, returning back to Canada to form The Headstones in 1987. It took the band a few years to get organized, but its blatant punk attitude found support from MCA Records who signed the band in 1992, releasing their debut album `Picture Of Health’ in 1993. Fuelled by radio support for “When Something Stands For Nothing” and “Tweeter And The Monkey Man,” The Headstones; now comprising of guitarist Trent Carr, bassist Tim White, keyboardist Steve Carr and drummer Jesse Labovitz released two more albums, establishing the band with a serious attitude that was universally loathed by their rivals. Flipping lit cigarettes at their audience didn’t help the band’s image.

Headstones 2014
Headstones Live 2014 – Photo by The Music Express

It was Dillon’s raw attitude which caught the attention noted Toronto-based film producer/director Bruce McDonald who cast him first as convicted murderer Clarence Gaskill in 1995 and then as Joe Dick band leader of Hard Core Logo in 1996. “Yes, Bruce saw something in me but so did (noted producer) Quentin Tarantino, (who bought the U.S rights to Hard Core Logo). It’s something I had all along, but music was always my first love”.

Sadly Dillon needed to walk away from music and movies to deal with drug and alcohol issues. Still, with the help of a supportive team featuring his loyal band, personal manager Bernie Breen and his wife Midora Fujiwara, he returned to show a new maturity as a performer in Durham County as troubled police officer Mike Sweeney for four seasons before featuring as Sgt. Ed Lane in Flashpoint which ran for five seasons.

Headstones Album - PeopleSkills on Vinyl
Headstones – Photo by Gordon Hawkins

“They saw something in me that was redeemable.” Dillon allowed. “A lot of it was beyond my control. I have been fortunate to be surrounded by long haulers.” He also notes that his convalescence has allowed him to adopt a more sophisticated attitude toward his songwriting. “I think all of that previous anger and angst has been re-channelled. I take pride in being a lot more mature.”

Since then, Dillon, has been featured in numerous movies and tv roles and turned a friendship with Sheridan into high profile roles in Yellowstone and Mayor Of Kingstown. But when you mention possible future Oscar or Emmy-winning roles, Dillon would rather produce a successful Headstones’ album.

Headstones Flight Risk Concert Dates
Headstones Flight Risk Concert Dates

Anticipating his current tour, Dillon enthuses that “By the time we hit Toronto, it’s going to be fun. We’ll be playing set pieces that we like, and the new album kills.” He is especially looking forward to playing at The Phoenix Concert Theatre on December 22nd. “I remember seeing Teenage Head there and The Tragically Hip there; the sight lines are great, the sound is great, the Phoenix along with Vancouver’s Commodore Ballroom and the Burton Cummings Theatre in Winnipeg are my favourite venues.”

For more tour information, please link to

Headstones November/December Tour Dates 2022

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